Venlafaxine hydrochloride

Names

[ Name ]:
Venlafaxine hydrochloride

[Synonym ]:
1-[2-(Dimethylamino)-1-(4-methoxyphenyl)ethyl]cyclohexanol hydrochloride (1:1)
Efectin
Venlafaxine Hydrochloride
Effexor
Venlafaxine HCl
MFCD03658865
EINECS 200-659-6
Cyclohexanol, 1-[2-(dimethylamino)-1-(4-methoxyphenyl)ethyl]-, hydrochloride (1:1)
Efexor
(±)-1-(a-((Dimethylamino)methyl)-p-methoxybenzyl)cyclohexanol hydrochloride
cyclohexanol, 1-[2-(dimethylamino)-1-(4-methoxyphenyl)ethyl]-, hydrochloride
RTECS GV8872760

Biological Activity

[Description]:

Venlafaxine hydrochloride is an antidepressant of the serotonin-norepinephrine reuptake inhibitor (SNRI) class.Target: SNRIVenlafaxine is an antidepressant of the serotonin-norepinephrine reuptake inhibitor (SNRI) class. First introduced by Wyeth in 1993, now marketed by Pfizer, it is licensed for the treatment of major depressive disorder (MDD), as a treatment for generalized anxiety disorder, and comorbid indications in certain anxiety disorders with depression. In 2007, venlafaxine was the sixth most commonly prescribed antidepressant on the U.S. retail market, with 17.2 million prescriptions.Venlafaxine is a bicyclic antidepressant, and usually categorized as a serotonin-norepinephrine reuptake inhibitor (SNRI), but it has been referred to as a serotonin-norepinephrine-dopamine reuptake inhibitor (SNDRI). It works by blocking the transporter "reuptake" proteins for key neurotransmitters affecting mood, thereby leaving more active neurotransmitters in the synapse. The neurotransmitters affected are serotonin and norepinephrine. Additionally, in high doses it weakly inhibits the reuptake of dopamine, with recent evidence showing that the norepinephrine transporter also transports some dopamine as well, since dopamine is inactivated by norepinephrine reuptake in the frontal cortex. The frontal cortex largely lacks dopamine transporters; therefore, venlafaxine can increase dopamine neurotransmission in this part of the brain. Venlafaxine interacts with opioid receptors (mu-, kappa1- kappa3- and delta-opioid receptor subtypes) as well as the alpha2-adrenergic receptor, and was shown to increase pain threshold in mice. When mice were tested with a hotplate analgesia meter (to measure pain), both venlafaxine and mirtazapine induced a dose-dependent, naloxone-reversible antinociceptive effect following intraperitoneal injection. These findings suggest venlafaxine's seemingly superior efficacy in severe depression as narcotics become increasingly used as a measure of last resort for refractory cases.

[Related Catalog]:

Signaling Pathways >> Neuronal Signaling >> Serotonin Transporter

Research Areas >> Neurological Disease

[References]

[1]. Bymaster FP, et al. Comparative affinity of duloxetine and venlafaxine for serotonin and norepinephrine transporters in vitro and in vivo, human serotonin receptor subtypes, and other neuronal receptors. Neuropsychopharmacology. 2001 Dec;25(6):871-80.

[2]. Goeringer KE, et al. Postmortem tissue concentrations of venlafaxine. Forensic Sci Int. 2001 Sep 15;121(1-2):70-5.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.394 g/cm3

[ Boiling Point ]:
397.6ºC at 760 mmHg

[ Melting Point ]:
207-209ºC

[ Molecular Formula ]:
C₁₇H₂₈ClNO₂

[ Molecular Weight ]:
313.863

[ Flash Point ]:
194.2ºC

[ Exact Mass ]:
313.180847

[ PSA ]:
32.70000

[ LogP ]:
3.83760

[ Storage condition ]:
Store at RT

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: GV8872760

CHEMICAL NAME :: Cyclohexanol, 1-(2-(dimethylamino)-1-(4-methoxyphenyl)ethyl)-, hydrochloride

CAS REGISTRY NUMBER :: 99300-78-4

LAST UPDATED :: 199801

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C17-H27-N-O2.Cl-H

MOLECULAR WEIGHT :: 313.91

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 235 mg/kg/12D-I

TOXIC EFFECTS :: Lungs, Thorax, or Respiration - fibrosis, focal (pneumoconiosis) Lungs, Thorax, or Respiration - acute pulmonary edema Gastrointestinal - other changes

REFERENCE :: JATOD3 Journal of Analytical Toxicology. (Preston Pub. Inc., POB 48312, Niles, IL 60648) V.1- 1977- Volume(issue)/page/year: 20,266,1996

Safety Information

[ Symbol ]:

GHS02, GHS06, GHS08

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H225-H301 + H311 + H331-H370

[ Precautionary Statements ]:
P210-P260-P280-P301 + P310-P311

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xi: Irritant;

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
26-37/39

[ RIDADR ]:
1230.0

[ RTECS ]:
GV8872760

[ Hazard Class ]:
3、6.1

[ HS Code ]:
2922509090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2922509090

[ Summary ]:
2922509090. other amino-alcohol-phenols, amino-acid-phenols and other amino-compounds with oxygen function. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%

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J. Chromatogr. A. 1418 , 140-9, (2015)

The fate and removal of organic micropollutants in the environment is a demanding issue evidenced by the recent European policy. This work presents an analytical method for the trace quantification of...

The antidepressant venlafaxine disrupts brain monoamine levels and neuroendocrine responses to stress in rainbow trout.

Environ. Sci. Technol. 48(22) , 13434-42, (2014)

Venlafaxine, a serotonin-norepinephrine reuptake inhibitor, is a widely prescribed antidepressant drug routinely detected in the aquatic environment. However, little is known about its impact on the p...

Enantiomeric fraction evaluation of pharmaceuticals in environmental matrices by liquid chromatography-tandem mass spectrometry.

J. Chromatogr. A. 1363 , 226-235, (2014)

The interest for environmental fate assessment of chiral pharmaceuticals is increasing and enantioselective analytical methods are mandatory. This study presents an enantioselective analytical method ...